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Soooooooo About that Trip to Chicago

I love to travel so when Jackie decided to go on an impromptu trip to Chicago for the weekend, I made it happen. I got Friday off of work, we rented a car and off we went. Some people thought we were nuts for driving when we were only going for the weekend but the whole road trip added to the experience. Yes, we got lost. Yes, we saw some creepy places. And you know what? It's just a whole heap of things we can now add to our travel memories.


The drive was supposed to be 8 or 9 hours but it ended up being 12! Yes, 12! I had borrowed an older GPS from my parents and while it worked great in Canada, we ran into some issues across the border. Unfortunately our GPS wasn't picking up all the route changes due to road closures and construction. Without our data on our cell phones, we struggled to figure it out but finally made it into Chicago right at their rush hour.

We had a few more hiccups with trying to find our spot, a beautiful studio we booked through AirBnB but once we were there we were beyond happy with the space. After we settled in, we roamed town for a bit and grabbed some food. By nightfall our homie Derrick had arrived and we chilled out and watched some movies before knocking out for the next day.


Saturday was our only full day in Chi Town and guess what? The weather was set to be cold, windy and rainy. I initially went out with my wool coat but turned back around to put on my winter jacket and layer in order to survive the chill. Regardless, we still had such an amazing day and fit in so much.

When we woke up we didn't rush, we actually were out the door around 11am but before that I made sure to plan our day out. After all, it was our only full day! I tracked all the areas each of us wanted to go on a map and then looked up how to get around. Day passes on the CTA sounded like a the best bet and off we were. We had to walk a bit to the closest station but we clearly enjoyed ourselves along the way. At least I did lol (as you can tell from the pictures)!

On our way to our first stop, we ended up in what looked like a business and financial district. Considering it was the weekend it was pretty desolate but it made for some pretty amazing shots like the one below.

We could already start to see the architecture that Chi Town is known for. Some areas reminded me of the MGM era in movies with that old school feel to it. The closest present day description I can give of that is Hollywood Studios in Disney World in Orlando, Florida. It was beautiful to see and it made me wonder what the city was like decades before.

We made the decision to eat some food before heading to our first spot so we stopped at a restaurant for some of that famous Chicago deep dish pizzas and hot dogs. Here's an interesting fact, they don't use ketchup (which I don't mind cause I don't like ketchup) in their hot dogs. Rather they have a ton of other toppings like onions, mustard, peppers, pickles, and tomatoes and relish. It was delicious and, truth be told, I had several hot dogs throughout the trip.

Once we were done eating we headed to Willis Tower which is the tallest building in the western hemisphere (according to their site). As Torontonians, this isn't anything major since our very own CN Tower held the record for tallest free standing building for many years and is considered one of the Seven Wonders of the Modern World. What was interesting about the Willis Tower was the SkyDeck. The best way to describe it is an enclosed glass balcony from top to bottom. You basically step out into it and you can see the whole city under your feet and around you. 

We were scared at first but ended up acting like clowns when it was our turn, even jumping on the glass at some point (Jackie has the photos at her place to prove it)! The weather was foggy so we couldn't see the city clearly but the experience was still beautiful. 

Once we came back down the tower, we ended up in the souvenir shop where they had fudge samples so we went nuts chowing down on some pretty awesome flavours (I'm actually not a fan of fudge but trust me when I say these flavours were amazing). After looking around I found a black fedora and I just couldn't leave without it! Enter in my little black hat that's going to appear in nearly every photo now.

On our way to our next sight, we had the chance to catch a train from Quincy Station which was a sight to see! I'd never seen a station so old and yet so beautiful. The station was built in 1897! Can you imagine that? I was walking up the same stairs, going through the same turnstiles, and standing on the same platform as someone else did nearly 120 years ago!!! That's insane! I was so fascinated.

Honestly, the train system was one of my favourite parts of Chicago because I found that not all stations looked the same. Some stations had such an interesting flare to them. I'd definitely go back and discover their system a little more.

The train rides were a joy in in itself. My classic gun fingers came out, but then again, when am I ever without them?


Once we got off the train we visited some bakeries we saw because Jackie loves all things pastry. She's actually a pastry chef by profession. Along the way we ran into some more awesome architecture like this alley way below.

We then headed over to Millennium Park which was full of tourists and hosted numerous sights and structures. While we were visiting there was actually two demonstrations/protests going on. The main one in our area was regarding an issue in Yemen and suddenly a slew of young kids with a Christian message came along chanting. It was interesting to see how the two groups collided and then went on their way. This is actually the second time I've travelled with Jackie and we saw a protest happening. The last time was when we got stranded in Istanbul, Turkey (which is a whole other topic) and we were shopping at Topshop in Taksim.

The first place we noticed at the park was this balcony type area that faced the centre of a major street. The next thing that caught my eye was the Jay Pritzker Pavilion which looked like bent metal sheets that waved and curved around each other. Of course, you can't come to Millennium Park without visiting Cloud Gate a.k.a. "The Bean" which was created by Anish Kapoor and has become a staple for tourists to visit in the Windy City.

When we were at the Bean there was a wedding going on at the time and I was so tickled by it so obviously I creeped them. Can you see me taking a selfies with them in the back and smiling like a little kid? I'll forever be a part of their love and they'll never know!

Our next stop was the Navy Pier. There was a little carnival area that was pretty empty, likely because of the weather. It was even colder at the pier because we were near the water and the wind had picked up. We still decided to get on the ferris wheel and brave the weather. I was perfectly fine through it all but poor Derrick was freezing his tail off.

I knew I couldn't come to Chicago without a shopping session so we went to a mall in the marina where I picked up an oversized black sweater with Chicago written on it. That wasn't enough for me though, on the way back to our place I had to go into one of the city's shopping districts and guess what store I ended up in? Yup, Topshop. I literally visit every Topshop I can when I travel. It's one of my favourite stores ever. While we were there I saw this interesting mirrored wall and I decided it was selfie time. I made it a rule for us to take selfie everyday just for fun.

After shopping was done we headed back to our spot to change for an improv show that Jackie's cousin and his crew were performing in. Leave it to me to make a lot of noise and comments while the performance was going on and almost get pulled on to the stage because of it (I'm not a heckler, I just play along)!

We didn't have set plans for after the show so we went for a drive and decided to go see the United Center and find the Jordan statue in the middle of the night. Jackie and Derrick tried to jump a fence to get closer while I stayed warm in the car before we went on to our next adventure.

Finally we ended up at a bar that was also an arcade. Pretty novel idea! We played some games, listened to some tunes and then grabbed some grub before it was time to head back.

Day 3

Our trip was so short but you would have never known considering all that we did. On Sunday we packed up and had breakfast down the street at this cute cafe we kept passing on all our trips out of our studio. After we spent the morning talking and eating some delish brekkie, it was a bittersweet goodbye as Derrick headed off to Ohio and we made moves towards Toronto.

We tried to go find some of the spooky places we got lost in when we were travelling to Chicago so that we could do a photo shoot. Unfortunately we were unsuccessful in finding those areas but we drove through some pretty deserted places like Gary, Indiana. It was eerie seeing some of these areas completely empty, like a ghost town. We saw so many run down hoods like that through out our drive. It's such contrast to what you would see driving in Ontario.

Oh, and if you were wondering, our trip back home was way shorter than our trip in, even with the detours we made.


All in all, I would definitely go back to Chicago in heart beat and spend a little bit more time getting to know the city, Our trip may have been short but we made such good use of our time so I'm happy about that. Oddly enough, while I'm typing this I'm actually getting prepared to pickup Jackie from the airport and guess what? She's flying into Toronto from Chicago O'Hare (she had her connection there) so until next time...



  1. Im amazed at how you placed our whole chicago experience our trip!


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